1H-1,2,4-Triazole → HCID 15036538, compound

HRID 1086149Notes

Reaction equation

HRID 1086149 reaction equation
[C:1]([C:3]1[C:4](=O)[NH:5][C:6](=[O:27])[N:7]([C@@H:9]2[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@@H:10]2[O:11][C:12](=[O:14])[CH3:13])[CH:8]=1)#[CH:2].[NH:29]1[CH:33]=[N:32][CH:31]=[N:30]1>N1C=CC=CC=1>[C:1]([C:3]1[C:4]([N:29]2[CH:33]=[N:32][CH:31]=[N:30]2)=[N:5][C:6](=[O:27])[N:7]([C@@H:9]2[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@@H:10]2[O:11][C:12](=[O:14])[CH3:13])[CH:8]=1)#[CH:2]

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 15036536HCID 15036536, compound

Product 1

HCID 15036538HCID 15036538, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5Ethynyl-1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)uracil from Example 5 (0.6 g, 1.5 mmol), 1,2,4-triazole (0.33 g, 4.8 mmol) and p-chlorophenylphosphodichloridate (0.8 ml, 4.8 ml) were stirred together in dry pyridine (20 ml) for 72 hr. The resulting dark solution was evaporated to dryness and the residue purified by column chromatography on silica eluting with ethylacetate/hexane (9:1) to give an apparently unsatable product (0.44 g) which was used in its crude from in the next stage of the synthesis.

Workup

  1. customThe resulting dark solution was evaporated to dryness
  2. customthe residue purified by column chromatography on silica eluting with ethylacetate/hexane (9:1)

Sources & evidence

ORD record
ord-47d55a56819e4b3789936095ce8e4226
Source dataset
uspto-grants-1991_07
Patent number
US05028596

Reaction notes

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